Provisioning a personal build

Friend of mine asked me an interesting question. He wanted to write an iOS utility solely for his own own use.

AFAIK he needs an Apple dev license to deploy an ad hoc build to his own device, and furthermore the app will stop running when his Ad Hoc provisioning expires, and worse, he won't be able to renew it once his dev licence runs out.

His options seem to be:
1) Get his app approved, put it on the store, buy it from himself, then remove it from the store. That copy will not expire.
2) I believe corporations can join a more expensive dev program ($250-$300?) that let's them build and deploy apps without going through the app store.
3) Jailbreak his device? Pirate his own app? I know little about how pirates break Apple's DRM, and would prefer to keep it that way.

These all seem like overkill for this particular use-case. Are there any better methods that a hobbyist could use to deploy apps to a device for his own personal use? I think this is relevant to this forum because I might very well want to carry a portfolio of WIP with me, without wanting to refresh the ad hoc build every few months.

Bonus points for any answer that manages to avoid impassioned rants about Apple's DRM. :-)

#1 is pretty clever, though as I recall, you have to keep renewing your developer account for an app to stay up on the store. I can't imagine apps from expired accounts would get deleted from people's devices, but it'd be a problem if he ever needed to redownload it.

Short of jailbreaking, I don't think there's a way this can be done without paying Apple. However, what if he were to piggyback on someone else's dev account? If he knows anyone who has a license and plans to keep renewing it, can spare a UDID for his device, and doesn't mind signing an ad hoc build of his app occasionally, that would do the job. I can see how it would get tiresome to have to make a new build every few months or so when the provisioning profile expires, but if money is the main issue, maybe that would be good enough? It could be automated enough to require only a few seconds of effort for the account owner.

I think there are some special requirements you have to meet to qualify for an enterprise developer account with its special provisioning, though I don't have any direct experience with it. If it costs that much more, it probably makes more sense to just use an individual account. Assuming an enterprise license costs $300 and (best case) would let him deploy an app that never expired, it would only make sense if he was going to run the exact same application 4 years from now without recompiling or downloading it again. Given Apple's history, I wouldn't be at all surprised if their hardware or OS changed enough that old stuff wouldn't run anymore, so it's a gamble either way.

For my friend's utility I suggested he sidestep the issue by making a web app and using his 3g device to access it.

He found yet another solution, which was to buy a util on the app store that does 90% of what he wants. Now he just has to beg the developer to add the other 10% :-/ I suggested that if he could talk the dev out of the source code, he could run it in the iOS simulator without provisioning, and offer his improvements back to the developer. Pretty sure you can get the SDK without paying the developer license fee. So that's another way one could to piggyback off another developer.